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Preparation method of imidazolyl acetonitrile compound

A technology of acetonitrile and imidazole, which is applied in the field of preparation of imidazolyl acetonitrile compounds, can solve the problems of unstable yield and unsuitability for industrial production, and achieve the effects of improving product quality, avoiding the use of high-risk reagents, and high yield

Active Publication Date: 2019-05-07
CHEMVON BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The technical problem to be solved by the present invention is to overcome the preparation method of the synthetic intermediate 2-(1H-imidazol-1-yl)acetonitrile of luliconazole in the prior art or the use of strong base NaH as the reaction condition, which is not suitable for industrialization The problem of production, or there is the problem of unstable yield, thus a kind of preparation method of imidazolyl acetonitrile compound is provided

Method used

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  • Preparation method of imidazolyl acetonitrile compound
  • Preparation method of imidazolyl acetonitrile compound
  • Preparation method of imidazolyl acetonitrile compound

Examples

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Embodiment 1

[0050] Example 1 Preparation of 2-(1H-imidazol-1-yl)acetonitrile

[0051] In a 10L three-necked flask, add 5L of acetonitrile and imidazole (1kg, 14.7mol), stir to dissolve them completely, and then cool to 0-10°C. Solid potassium carbonate (1.0 kg, 7.25 mol) and solid KOH (0.5 kg, 8.9 mol) were added. Chloroacetonitrile (1.2kg, 15.9mol) was then added dropwise to the reaction system at a rate to keep the system temperature between 0-5°C. After the addition, the reaction of raw materials is completed. Filter to remove the filter residue, pass through the filtrate with hydrogen chloride gas to precipitate a large amount of solids, and filter to obtain the hydrochloride salt of 2-(1H-imidazol-1-yl)acetonitrile. Then use 5L DCM to beat the wet product, then feed ammonia to make the pH of the system reach 9-10. Filter to remove insoluble matter, evaporate the organic phase to dryness under reduced pressure, add 5 L of methyl tert-butyl ether, cool to below -20 degrees, a large ...

Embodiment 2

[0052] Example 2 Preparation of 2-(1H-imidazol-1-yl)acetonitrile

[0053] In a 10L three-necked flask, add 5L of acetonitrile and imidazole (1kg, 14.7mol), stir to dissolve them completely, and then cool to 0-10°C. Solid potassium carbonate (1.2 kg, 8.7 mol) and potassium hydroxide (0.6 kg, 10.7 mol) were added. Chloroacetonitrile (1.2kg, 15.9mol) was then added dropwise to the reaction system at a rate to keep the system temperature between 0-5°C. After the addition, continue the reaction until the raw material disappears completely. Filter to remove the filter residue, pass through the filtrate with hydrogen chloride gas to precipitate a large amount of solids, and filter to obtain the hydrochloride salt of 2-(1H-imidazol-1-yl)acetonitrile. Then beat the wet product with 5LDCM, then feed ammonia to make the pH of the system reach 9-10. Filter to remove insoluble matter, evaporate the organic phase to dryness under reduced pressure, add 5 L of methyl tert-butyl ether, cool...

Embodiment 3

[0054] Example 3 Preparation of 2-(1H-imidazol-1-yl)acetonitrile

[0055] In a 10L three-necked flask, add 5L of acetonitrile and imidazole (1kg, 14.7mol), stir to dissolve them completely, and then cool to 0-10°C. Solid potassium carbonate (1 kg, 7.3 mol) and solid KOH (1 kg, 17.8 mol) were added. Chloroacetonitrile (1.2kg, 15.9mol) was then added dropwise to the reaction system at a rate to keep the system temperature between 0-5°C. After the addition, the reaction of raw materials is completed. Filter to remove the filter residue, pass through the filtrate with hydrogen chloride gas to precipitate a large amount of solids, and filter to obtain the hydrochloride salt of 2-(1H-imidazol-1-yl)acetonitrile. Then use 5L DCM to beat the wet product, then feed ammonia to make the pH of the system reach 9-10. Filter to remove insoluble matter, evaporate the organic phase to dryness under reduced pressure, add 5 L of methyl tert-butyl ether, cool to below -20 degrees, a large amou...

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Abstract

The invention discloses a preparation method of an imidazolyl acetonitrile compound. The preparation method comprises the following steps: performing a substitution reaction shown in the description on chloroacetonitrile and imidazole in a solvent in the presence of an alkali, so as to prepare the compound, wherein the solvent is acetonitrile, and the alkali is a mixture of potassium carbonate andpotassium hydroxide, wherein a mass ratio of the potassium carbonate to the potassium hydroxide is 1:1 to 5:1. According to the preparation method provided by the invention, luliconazole intermediate2-(1H-imidazol-1-yl)acetonitrile with a yield of 95.5% and purity of 99.5% can be obtained by the preparation method; and the preparation method is simple and convenient to operate, the yield is remarkably improved, usage of high-risk reagents is avoided, the product quality is improved, and the method is very suitable for industrialized production.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a preparation method of imidazolyl acetonitrile compounds. Background technique [0002] Luliconazole (English name: Luliconazole) is a new type of imidazole topical antifungal drug. It is a lanoconazole analogue. Synthesis and fungal growth. In addition to being used for the treatment of tinea pedis, jock itch and tinea corporis, it has also been developed for the treatment of onychomycosis (ononychomycosis), and has entered phase III clinical trials. [0003] Luliconazole was originally developed by Nihon Nohyaku Co., Ltd. In November 2013, the US FDA approved 1% luliconazole cream for external use to treat interdigital tinea pedis, jock itch and tinea corporis. The product name is Luzu, which was first launched in North America. As early as April 2005, luliconazole was approved for marketing in Japan, and the trade name was Lulicon. It was launched in India and China in ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/56
Inventor 王方道吴伟锋王猛王东缪华兵苏奇峰
Owner CHEMVON BIOTECH CO LTD
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